Why is Portland considered a strange city?

Portland has developed, and then cultivated, a decidedly quirky vibe. With businesses like Voodoo Donut, Powells City of Books, the world's smallest park (Mills End Park, look it up), the unicycle guy with the darth vader helmet playing bagpipes, etc, etc its a town that leans heavily into the leftist counter culture thing 

because there really wasnt a ton of planning that went on early on.

Downtown portland is a MESS

Maine is a strange state!!

Maybe you are referring to the "Keep Portland Weird" philosophy?

Some highlights include: 

Portland's weirdness eccentricities include the Voodoo Doughnut shop, the World Naked Bike Ride, the Zoobomb cycling events, artist Adam Kuby’s (now removed) Portland Acupuncture Project, the popularity of yarn bombing, the Portland Urban Iditarod, and the now-defunct Velveteria Museum of Velvet Paintings and 24 Hour Church of Elvis.  Another is the "Horse Project" (small model horses reined to curb mounted loops from the 1800s). The first "Keep Portland Weird festival" was held in October 2007 at the Central Library, and among the participants were the Portland Ukulele Association, Free Geek, and the Portland Area Robotics Society. Another took place in November 2009.  Portland's city commission government—a type of municipal governance now rare in the U.S.—has been described as another aspect of its weirdness, compounded by the various peculiarities of its implementation.

Portland is the largest U.S. city which does not fluoridate its water.  Voters have rejected four attempts to do so—most recently in 2013—due to concerns of adding "fluoridation chemicals" to one of the most pristine water supplies in the world.

Which state?  There's more than one.